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Apartments in Province of Siena and Houses – Holiday Lettings - Holiday Rentals Province of Siena

3,478 Holiday homes

Private room rental in Poggibonsi

Poggibonsi private room

1 bedroom • 1 bathroom • sleeps 2

from £53 / night

£336 / week

1 / 18

Holiday apartment in Pienza

Pienza apartment

2 bedrooms • 1 bathroom • sleeps 4

from £77 / night

£528 / week

1 / 13

Montalcino holiday farmhouse accommodation

Montalcino farmhouse

3 bedrooms • 3 bathrooms • sleeps 8

from £346 / night

£2,418 / week

1 / 45

Holiday home in Bagni di San Filippo

Bagni di San Filippo house

1 bedroom • 1 bathroom • sleeps 4

from £62 / night

£430 / week

1 / 15

Holiday home with shared pool in San Gusme

San Gusme house

3 bedrooms • 3 bathrooms • sleeps 8

from £250 / night

£1,660 - £2,456 / week

1 / 26

Holiday apartment in Siena

Siena apartment

1 bedroom • 1 bathroom • sleeps 3

from £77 / night

£672 / week

1 / 20

Holiday home rental

Siena house

1 bedroom • 1 bathroom • sleeps 4

from £96 / night

£576 / week

1 / 11

Holiday apartment in Siena

Siena apartment

2 bedrooms • 1 bathroom • sleeps 5

from £104 / night

£726 / week

1 / 25

Holiday home in Montepulciano

Montepulciano house

3 bedrooms • 3 bathrooms • sleeps 6

from £149 / night

£960 / week

1 / 18

Holiday home with swimming pool in Radda in Chianti

Radda in Chianti house

8 bedrooms • 5 bathrooms • sleeps 16

from £329 / night

£4,735 / week

1 / 54

Montefollonico holiday home rental

Montefollonico house

2 bedrooms • 1 bathroom • sleeps 4

from £72 / night

£504 / week

1 / 32

Holiday b&b in Pianella

Pianella b&b

6 bedrooms • 15 bathrooms • sleeps 20

from £87 / night

£605 / week

1 / 7

Apartment rental in Montefollonico

Montefollonico apartment

1 bedroom • 1 bathroom • sleeps 2

from £60 / night

£384 / week

1 / 20

Apartment rental in Siena

Siena apartment

2 bedrooms • 1 bathroom • sleeps 6

“Truly a home away from home” The apartment is just as beautiful as the photos. It is 10km out of sienna but there are supermarkets, cafes etc within 3km. Andrea was the perfect host answering any questions promptly when we emailed him. The apartment was stocked with breakfast products for our first few days like jam, toast, croissants, coffee, tea, sugar and oils which was much appreciated. Beautiful surroundings and very comfortable property. Could not find fault with anything. Thank you Andrea.

from £91 / night

£557 - £720 / week

1 / 25

Apartment rental in Montepulciano

Montepulciano apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £135 / night

£864 - £1,025 / week

1 / 18

Condo rental in Siena

Siena condo

1 bedroom • 1 bathroom • sleeps 4

from £89 / night

£618 / week

1 / 18

Val d'Orcia holiday b&b rental

Val d'Orcia b&b

3 bedrooms • 3 bathrooms • sleeps 6

from £149 / night

£1,041 / week

1 / 16

Holiday apartment rental

Poggibonsi apartment

2 bedrooms • 1 bathroom • sleeps 4

from £58 / night

£403 / week

1 / 15

Holiday home in Colle di Val d'Elsa

Colle di Val d'Elsa house

1 bedroom • 2 bathrooms • sleeps 3

from £87 / night

£603 / week

1 / 17

Holiday farmhouse with shared pool in San Gimignano

San Gimignano farmhouse

1 bedroom • 1 bathroom • sleeps 2

from £82 / night

£528 / week

1 / 18

Holiday apartment in Bettolle

Bettolle apartment

2 bedrooms • 1 bathroom • sleeps 4

from £68 / night

£384 / week

1 / 7

Holiday villa in Monteroni d'Arbia

Monteroni d'Arbia villa

2 bedrooms • 1 bathroom • sleeps 3

from £39 / night

£269 / week

1 / 6

Apartment rental in Castelnuovo Berardenga

Castelnuovo Berardenga apartment

1 bedroom • 1 bathroom • sleeps 4

from £60 / night

£417 / week

1 / 21

Holiday apartment accommodation

San Gimignano apartment

2 bedrooms • 3 bathrooms • sleeps 3

from £63 / night

£437 / week

1 / 38

Holiday apartment in Siena

Siena apartment

1 bedroom • 1 bathroom • sleeps 5

from £87 / night

£605 / week

1 / 7

Home rental in Radda in Chianti with swimming pool

Radda in Chianti house

11 bedrooms • 8 bathrooms • sleeps 22

from £438 / night

£6,306 / week

1 / 54

Barn rental in Sovicille with shared pool

Sovicille barn

1 bedroom • 2 bathrooms • sleeps 4

from £77 / night

£518 / week

1 / 19

Penthouse rental in Siena

Siena penthouse

1 bedroom • 1 bathroom • sleeps 4

from £144 / night

£768 / week

1 / 40

Townhouse rental in Sovicille

Sovicille townhouse

2 bedrooms • 1 bathroom • sleeps 4

from £63 / night

£437 / week

1 / 17

Castiglione D'Orcia holiday apartment rental

Castiglione D'Orcia apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £106 / night

£336 / week

1 / 26

Holiday home rental

Montisi house

3 bedrooms • 2 bathrooms • sleeps 5

from £154 / night

£1,075 / week

1 / 18

Apartment rental in Montepulciano

Montepulciano apartment

2 bedrooms • 1 bathroom • sleeps 6

from £68 / night

£384 - £672 / week

1 / 36

Holiday apartment accommodation

Radicondoli apartment

2 bedrooms • 1 bathroom • sleeps 4

from £116 / night

£720 / week

1 / 22

Pienza holiday farmhouse rental

Pienza farmhouse

9 bedrooms • 8 bathrooms • sleeps 17

from £70 / night

£491 / week

1 / 40

Holiday farmhouse in Cetona

Cetona farmhouse

2 bedrooms • 2 bathrooms • sleeps 5

from £68 / night

£470 / week

1 / 4

Holiday apartment in Radicondoli

Radicondoli apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £86 / night

£624 / week

1 / 47

Townhouse rental in Siena with shared pool

Siena townhouse

1 bedroom • 1 bathroom • sleeps 3

from £116 / night

£806 / week

1 / 31

Casole d'Elsa holiday apartment rental

Casole d'Elsa apartment

2 bedrooms • 1 bathroom • sleeps 5

from £68 / night

£470 / week

1 / 15

Holiday apartment in Costalpino

Costalpino apartment

1 bedroom • 1 bathroom • sleeps 2

from £68 / night

£432 / week

1 / 12

Holiday apartment in Bettolle

Bettolle apartment

1 bedroom • 1 bathroom • sleeps 2

from £58 / night

£365 / week

1 / 9

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Top Destination reviews

Charming Cottage in Peaceful Country Setting - Sleeps 6
Beautiful setting in Tuscan countryside near Montepulciano

We rented the main living area of this apartment with a loft bedroom upstairs. It's in a lovely setting in the Tuscan countryside surrounded by vineyards and beautiful scenery. It is so peaceful and quiet; a nice respite after a more hectic visit to Florence. Laura was an excellent host making sure we had everything we needed. The apartment was very clean and lovely inside with exposed beams in the ceiling and tastefully decorated. The patio in the back was a relaxing to sit and view the surrounding landscape. If we visit Tuscany again we will be certain to stay here again.see more
**RATED REDUCED FOR SUMMER MONTHS* Exquisite 7 bedroom property - Private Pool
Great for our family gathering

This is a beautiful villa in Tuscany. We had a large family gathering for a week in June and it was the perfect spot for us. Exceptional Villas organised a chef to cook for us some nights and that was a great experience. True Italian food in Tuscany! The surroundings of the villa are stunning and we really got a true taste of Tuscan life. Looking forward to coming back again next year.see more
Monache 4 Farmhouse holiday rental with private pool and garden in San Gimignano
This was a grower!

I wasn’t certain that we had booked the right place when we first arrived. The property is oddly named as a farmhouse but is actually the basement and ground floor of a converted convent with the upper floors of the convent occupied by local Italian families. They however kept their shutters firmly closed all day to keep the heat out and as a consequence you are never even aware of them. The apartment (number four) was very clean and well presented. It was a little light on cooking kit (no serving bowls for example) and one or two of the five beds were not very comfortable. Elisabetta and Massimo could not have been more helpful or friendly if they had tried. They have a little shop near the reception area stocked with emergency essentials and there was also a large supply of great quality free vegetables including potatoes, garlic, Onions and fantastic tomatoes. The nearest shop is a 15 minute drive away in Montaione Coop (poor) or Castelfiotentino Lidl etc (Much better) so the Little honesty shop is a good option if you just need a couple of things. The pool is a nice size, chlorine, about 2/5 To a half is shallow-ish for children. Each apartment has an allotted good quality umbrella and sun loungers and seating. Whilst the view from summer parts of the garden across the valley is very beautiful, there is no actual view from the pool area due to the hedges which are presumably there to stop the wind. That said, I was quite surprised by the largish electric pylons striding down the hill! If you look closely in the photos, you can see the power lines. Oddly, you stop noticing them very quickly! We met lovely family is from Poland and Germany and hope to keep up with them! The children all played together really happily and communicated in English. All in all, we had a very relaxing time and were sad to leave.see more
Villa with private pool, air conditioning, quiet area & nice views 3km from town
Comfortabel and pleasant stay

Nice house on hillside with beautiful view into the valley. All bedrooms are equipped with airconditioning so your sleep is with windows closed ( no mosquitoes and comfortable temperature). We stayed during a very hot period in july but had good night rests. Almost every day in the early afternoon a breeze from the west is cooling down the house. Good wifi coverage , also down at the pool. Supermarket ( middle size COOP ) is downtown at about 10 minute drive. We had fresh tasteful tomatoes and vegetables from the garden and one evening Mr Rafaelle prepare a pizza diner for us , made by his friend and family in the pizza oven behind the garden house. What a wonderful Italian experience was that! We had easy communication through cellphone text messages.see more
Beautiful apartment with pool and great views of San Gimignano
The most wonderful stay in San Gimignano

We had a fabulous week in this stunning property. The owners were very hospitable and were able to book us in at very short notice. The apartment is very clean and well equipped with everything you need. The location is perfect to explore Tuscany, with amazing views of San Gimignano and we were recommended some great local restaurants and wineries. Thank you so much for sharing your apartment and will definitely visit again!see more
- LA CASA DEI NONNI - Only you and your family
Only Wxcellent

The house is charming, spacious, extremely well fitted out and super clean (I am extremely fussy) so believe me it was beautifully clean and comfortable. The beds are comfortable and the bathroom was just fine. It was I loved everything about this house. The views were spectacular. Two bedrooms are beautiful. The owners are wonderful hosts who go above and beyond to make you feel welcome. . Just sitting on the balcony, verandah or around the pool with the amazing views is all you need to do but it’s also a great base to explore other Tuscan towns. Recommend that you have a car. Just Wow.see more

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